


Experiences

by HeathenVampires



Category: How to Train Your Dragon (Movies)
Genre: Anal Play, Anal Sex, Curious Eret, Explicit Sexual Content, F/M, First Time Bottoming, Friends With Benefits, Horny Astrid, Modern AU, Pegstrid, Sex Toys
Language: English
Status: Completed
Published: 2019-04-07
Updated: 2019-04-07
Packaged: 2020-01-06 06:48:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,477
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18383162
Author URL: https://archiveofourown.org/users/HeathenVampires/pseuds/HeathenVampires
Summary: Astrid was gossiping about a recent one night stand, and the adventurous escapades he hears about have Eret very intrigued. And a little scared.





	Experiences

**From a prompt on tumblr! (sorry it took me so long to get to, and so long to put on AO3 oops)  
**

**Basically, Eret, Astrid and the theme of anal sex. Contains, amongst other things, pegging.**

-HTTYD-

"Wait, hold on. You can't just drop 'I did him in the ass' and move on with no finer details. Back up!"

Astrid laughed, stretching out along her sofa and reaching for another chocolate from the pile next to her. She was currently updating Eret on her latest one night stand, and apparently it had been quite the adventurous night. The way her eyes sparkled as she relayed the evening certainly said she'd had _fun._

"After like, round two... or three, if we count some serious oral, I was getting a condom out of his drawer cus I only had two on me. Then I dropped it, and when I went to get it I found the treasure chest under his bed."

Eret nodded, vaguely concerned for the safety of the guy Astrid had hooked up with. She was all but feral, he knew - he'd seen the marks on her ex boyfriends, where Astrid had bit or scratched them in the heat of passion.

"Is that what you call it?"

"Hey, they were _his_ toys. I'm not denying the box was smaller than mine, but it was still there!"

"And so naturally, you invaded the box?"

Astrid nodded.

"I did ask first! He seemed a little surprised at first, but then the box was out and oh boy, we had fun. It's always the quiet ones!"

Eret rolled his eyes, snagging a chocolate while Astrid reminisced. She glared, then resumed waxing poetic about the guy. So far, Eret only knew that he had freckles, messy hair and a box of sex toys.

"At what point did this become you doing his ass?"

"He had a strap on kit in there. I asked if he'd used it before, he said yes. I wanted a go! So we traded. My ass for his. After I tested out his handcuffs and vibrators... honestly, I got _no_ sleep that night. Had to go to work the next day on coffee, a rushed shower and in borrowed boxer shorts. _Damn,_ worth it though."

Only Astrid could make such a night sound so effortlessly casual, as though most guys wouldn't rather eat a bullet than have someone peg them, although he imagined the fact Astrid offered _him_ anal sex too probably eased the way...

"It was a one night stand, so basically, you _stole_ his underwear?"

"If I see him again he can come get it back. Then I can show him _my_ toys."

"You're terrible."

"You love me. And a good time was had by all. He seemed pleasantly surprised I was into it, to be honest. I get the feeling not all girls are willing to top him."

"Well, most guys aren't in to getting anything up the ass, fake or real."

Astrid rolled her eyes.

"Then you are missing out. Seriously, that was probably when he came the hardest all night. And that includes after I blew him for... a solid twenty minutes."

Eret frowned.

"Somehow, I think I'll live."

His sex life was just fine without anyones butts being involved. Well... mostly. He was in something of a dry spell. Which was the explanation Eret was going with as he tore his eyes away from Astrid's stomach, exposed skin as she stretched herself out with a contented sigh. He wasn't blind; his best friend was _hot,_ but it was a line never crossed. A friendship he valued over the occasional wayward wondering.

"Suit yourself."

"Why, you offering?"

Eret regretted the words the instant they left his mouth, but he and Astrid had too much of a back-and-forth banter to stop himself thoughtlessly answering. Astrid's eyes lit up with his words, and Eret knew there and then he was in trouble.

"Maybe."

Astrid's tone wasn't a dead giveaway either way - she could easily be dead serious or absolutely kidding. The smirk playing across her lips could be playful mischief or lusting anticipation. There was no way to be sure with Astrid.

"Maybe?"

"Hey, you're cute. I wouldn't kick you outta bed, but if you're not on board I'm happy to go find another victim."

"Astrid, quit fooling around."

Was it warm in there? Was she sitting closer? Or was Eret just imagining things?

"I'm not. Well. I suppose I'm _offering_ fooling around. Gods, I didn't realise there _was_ a guy this hesitant about getting in my pants."

"We're best friends, this is... more than that."

"Only if we make a big deal about it."

Astrid was looking increasingly serious about it, and Eret was seriously considering agreeing. His cock already did, filling out at the idea of getting anywhere _near_ Astrid's pants right now. Oh gods, she was going to notice and call him a pervert, surely.

"So... you're suggesting we just..."

"Fuck. You can say it."

"Right. And nothing else changes?"

Brushing blonde hair out of her eyes, Astrid nodded.

"Yep. I don't see why anything would have to, unless you turned into a creep who thought he could get it off me whenever. _Then_ we'd have issues."

Eret tried to dissuade his wayward cock with the reminder Astrid had offered on the _condition_ she got to 'top' him first. Somehow, it wasn't working, a twitch of curiousity only adding to it. Eret was an open-minded guy usually, but still...

"You know I'm not like that."

He was stalling.

"I do. But I don't know if you're up for it for real, or just playing along. So" Astrid got up, and she was definitely closer now. In his lap, specifically, leaning in so close he could smell the chocolate on her breath "I'll ask you straight. Up for it?"

Since she was literally sat on his lap, Astrid had to know at least part of Eret was _very_ up for it. But she didn't actually push for anything. Let Eret decide.

_Screw it._

"Yeah."

Astrid kissed him. She'd done that before, playfully or drunkenly or both, but this time was sober, intentional, with the weight of Eret's erection digging into her. It took him a minute to realise, but when he responded Astrid wriggled closer, straddling his lap properly as her tongue slid into his mouth.

Somehow, Astrid had led him to her bedroom. Eret was still not certain he wasn't dreaming, at least when she pulled him down onto the mattress, rolling on top of him as she resumed kissing him senseless. He was much taller, broader than Astrid, but even so he felt very much 'held in place' as she climbed up his body, tugging up his top.

_Fuck, this might actually be happening._

His mind was a little hazy - Astrid could _kiss_ \- but Eret managed to wriggle out of the article of clothing, felt hands on his chest immediately. Astrid had seen his tattoos dozens of times before, had been there in the studio when some of them were done. But she'd never touched them like she was then and there, tracing fingers over lines and smirking as Eret shivered when her nail just dragged across his nipple, light enough not to really _hurt_ but sharp enough to almost make his toes curl.

"Think I can trust you to go first?"

First? Eret struggled to remember what she was even talking about, stomach doing a backflip when it came back to him. He had to think pretty seriously about it for a minute, as he was admittedly still a little terrified of the idea.

But then, he also trusted that Astrid wasn't looking to actually _hurt_ him, and she was placing a lot on Eret too by letting him take a turn on her after.

"Uh-huh."

Astrid quirked an eyebrow, lips quirked up in a pretty little pout as she contemplated him.

"Alright then. I'm holding you to it."

His hands were numb, took time to respond to the clear invitation to undress Astrid. He'd seen her in less than most people had - at least, most people she hadn't fucked. But it was so different when she was flushed and squirming, biting at his mouth, tugging at his belt. Knowing Astrid was a hungry, feral lover was one thing, _experiencing it_ was another entirely. She'd stripped him down to his boxers before she slowed, peering down as she tugged down the waistband to free his erection.

"Oh hello, _you've_ been holding out on me."

"Huh?"

"Pretty sure when we had the size discussion, you described yourself as average. _This"_ Astrid gripped his cock, squeezing "is not average."

Fighting not to buck needily into her grip, Eret tried to appear nonchalant.

"Well, I didn't want to sound conceited."

"Mhmm. Well, you'll have to go slow at first with me."

Astrid was already taking off her underwear, and Eret's eyes were rather glued to her bared torso. Figuring he wasn't exactly showing himself in the best light by being so inactive, Eret ran his hand up her thigh, gratified to find her slick and aroused already. He'd been a little worried their friendship would make everything too awkward for her to get turned on, but he quickly discovered that wasn't the case. Her hips rolled up into his touch, making sinful little noises in response that went right to his cock. When he reached down, trying not to rush but equally eager to get on, Astrid stopped him.

"What's wrong?"

"Oh, yeah, never done. Hold on" Astrid batted his hand away, shimmying up her bed to root around "yeah, here."

Condoms and lube bottle tossed at Eret, Astrid was already rolling on to her front, rising up on all fours and throwing Eret a smouldering look over her shoulder.

"Well? What are you waiting for?"

Well, she clearly wasn't patient about it. Eret wasn't surprised, somehow, knowing Astrid as well as he did. Still, she ought to give a man a minute to adjust to the sight of her ass just pointed up at them, wiggling invitingly, a few little freckles littering an otherwise blank curve. His mouth went dry as he remembered Astrid talking about sunbathing naked, though she wasn't currently sporting much of a tan.

Coating his fingers in lube - fingers first seemed like a good idea, and Astrid had mentioned being fingered in her ass before - he touched the tight little muscle, watching a light shiver run through Astrid, glancing up to see her biting her lip, watching him closely.

"Go on. I'm good."

His finger slipped in surprisingly easy, Astrid letting out a soft keening sound and pushing back, urging him on. Eret moved it a few times first, adding a second at her insistence, pushing them back and forth and feeling the tight muscles start to open up to him. Still in some disbelief that this was happening - his dry spell was ending, and it was ending in his best friends ass apparently - Eret kept working to loosen her, figuring it couldn't hurt since she'd commented he was big.

"Uhhh, come on Eret! I'm ready!"

"Are you sure? Don't want this above-average of mine to hurt you."

Astrid actually laughed, shaking her head before arching her back and mewling.

"I'm fine. Now either fuck me or bend over, cus I'm done waiting."

Well, Eret couldn't really ignore such an invitation. After wiping his hand clean to avoid slippage and shifting closer, he tore open the condom and rolled it down, glad to see it actually fit him properly. He added more lube, since he couldn't get her wet to ease the slide like he would normally. Astrid's knuckles strained slightly against her bed when Eret pressed against her, panting from both of them as he began to press in. He still couldn't quite believe it, even watching his cock disappear into Astrid inch by inch. After the initial resistance against the wider head, the rest of him slipped in with relative ease, Astrid gasping and twitching the whole way until Eret came flush to her cute little ass, the tight, hot grip feeling like it could squeeze the air from his lungs.

"Gods you're big... give me a minute."

"Should I-"

He began to withdraw, concerned, but Astrid reached back and gripped the side of his thigh, stilling him.

"Just stay _still_ for a second. Fuck, that's intense."

Eret complied, feeling the flexing of her muscles as they worked to adjust, rubbing the side of her hip in an attempt to soothe her. It was tempting to just _fuck,_ with the tempting heat and the _tightness_ that was incredible, but he could wait.

"Ok. G-go slow."

He did, pulling back only a few inches before he thrust back in, the powerful grip almost enough to drive him to insanity. Astrid gasped, letting out soft little whines with each of his thrusts at first, obviously getting used to it.

"So, feel like you've been missing out yet?"

"Uhhhh, yeah."

Eret was definitely ranking anal sex as a future possibility already, watching his cock disappear into her lithe body, feeling the way her whole frame shuddered with each thrust. Astrid bucked and moaned, encouraging him to move a little quicker. He increased his pace gradually, not wanting to just lose his mind to the feel of her, the sensations of her clenching at his cock so perfectly probably enough to break a weaker man than him.

Actually, it would probably break him too.

"C'mon Eret, I can take it!"

Warily keeping an eye on her at first, Eret moved with more purpose, thrusting harder and _gods_ she responded, swearing loudly and pushing back to meet his thrusts, lowering down to support her weight on one arm so her other hand could slide down to play with herself. The mental image was enough to make Eret shake, the added tremors in Astrid's body as she responded to both his touch and her own adding to his temptation to break and come, but damned if Eret was going to not hold back until she came too.

The harder her fucked her, the more vocal Astrid grew, body rocking with the force as Eret leant forward to reach her chest, groping at a flushed, sensitive breast and hearing Astrid make the most sinfully erotic sounds in response, his arm wrapping around her middle to hold her to him now he'd found his stride - they were employing a favourite position of his, even if it was in a way he wasn't used to, and Eret wanted to hit her deeper, expose more skin for his free hand to reach.

"Oh fuck... Eret!"

Hearing Astrid cry his name as her body convulsed, the spasming of the muscles still clutching his cock telling him she was in the throes of climax, was an experience Eret never expected to go through - and it was _hot_.

Gratified to have brought her off at last, Eret kept thrusting until he found his own release, hips stuttering as he filled the condom and reluctant to pull out of Astrid's warm, welcoming body even when he was done. She began to shift as he softened though, prompting Eret to let her down so he could pull out, holding the condom and hearing her let out a soft sigh of discomfort as he did so.

"You ok?"

"Mmm. That was awesome. You've really never done anal before?"

Eret nodded, shrugging.

"Never seen the appeal. Never been offered it either."

"Well, generally women don't mind if you _ask,_ but they'll mind if you push for it."

"I get it. Not for everyone."

Astrid nodded, rolling on to her back and stretching her arms up over her head, clearly still content in her nudity and uncaring that she was the subject of Eret's somewhat furtive glances.

"You should go clean up. Properly. I intend on putting my mouth on your cock and would rather it didn't taste like spermicide."

Oh fuck, right. They were trading. Eret wondered if he was about to chicken out, but then he remembered how Astrid had taken him - and climaxed from the feeling, not to mention responded like she was having quite a lot of fun. Then there was that itch of curiousity, after she described the guy she'd hooked up with recently...

"Right."

Eret ambled off to her bathroom and ditched the condom, rinsing himself off properly in the sink, digging out his wash bag - he had one there, Astrid had one at his place, in case of impromptu overnight stays - and running a cloth over himself a little self-consciously. Feeling cleaner and a little more terrified, he headed back out. Astrid was knelt on her bed, scrunched up towel resting on the top of her dirty washing basket, so he figured she'd cleaned excess lube off herself while he was gone.

"I have like, three different sizes that'll fit my strap-harness. You can pick."

It didn't take long for Eret to choose the _smallest,_ though even that wasn't miniscule. Astrid clearly liked her toys with a generous girth to them. Or maybe the smaller ones wouldn't fit her harness. He was overthinking it.

"RIght. Uh. Now what?"

"Now you come here. I don't want you getting all tense."

Astrid drew him back to the bed, kissing him until Eret was sufficiently distracted, though only for the time she spent actually pressed against his mouth. Hoping to delay - and explore - a little, Eret moved his mouth downward and Astrid let him, making those hot little sounds again when Eret mouthed at her chest, flicking his tongue over her nipple, palming her other breast.

"N-nice as that is" she pried him from her breast firmly "you aren't getting out of at least trying. I swear I'm not gonna rush and hurt you, and I reckon you'll forget to be nervous once I find your prostate."

He doubted _that_ very much.

"And if I don't?"

"If you're really not into it at all, then I'll give you head and we'll call it quits."

Worst case scenario, he got a blowjob? Eret could live with that.

"Alright."

Astrid grinned, pushing him down on his back and retrieving her lube bottle from where he'd dropped it earlier. It wasn't too weird when she knelt between his legs, hand pumping his soft cock until it began to firm up and swell in her hold. Nor was it too strange for her to shimmy down until she was on her stomach, tongue sliding up the underside with a smirk of pure mischief across her lips.

Her fingers, coated in slick lubricant, brushing up against his ass? That was definitely weird. It didn't feel terrible, but he couldn't say it felt all that nice either. Astrid kept playing with his cock, mouth and tongue slowly working their way around his shaft, staying away from the more sensitive head. When her finger finally breached him, Astrid took his tip in her mouth, sucking ardently and admittedly, it was a pretty good distraction. Her finger didn't hurt, really, it was just... odd.

Astrid kept sucking his cock, working her finger back and forth a few times, waiting for Eret to stop tensing up before she pushed deeper. He could feel her... searching, a little, wiggling her finger a bit before seeming satisfied as she touched-

"Oh, fuck!"

His hips bucked, effectively shoving himself deeper into Astrid's mouth and she had to back up, coughing slightly for the intrusion.

"Shit, sorry. Are you ok?"

"Yeah" she coughed again "fine. If you do that on purpose, I'm biting, fair warning. Guess you felt that?"

Eret nodded, half-certain he'd actually come from that sudden zap that ran through his body, liquid pleasure sliding through his blood and wondering if it would feel that good a second, third, fourth time it was touched.

"See, told you you'd be fine."

Astrid added a second finger to the first, pushing them back in and _yes,_ that was better, more of those waves of wonderful feelings washing over Eret as she worked him, not even needing to distract him with oral now. He couldn't seem to stop squirming, fighting not to push down on her fingers for more of... just _more._

She began to push her fingers deeper, obviously intending to make it easier for Eret to take her properly. It was remarkable how quickly she'd converted him; almost embarassingly fast, but Eret was feeling too good to care, his cock leaking with the insistent pleasure. His arousal kept climbing, Astrid's eyes keenly observing his reactions.

"You ready?"

Eret wasn't sure he could verbalise 'I'm ready', but he could nod, could work to stay relaxed while Astrid attached the strap-on to her body, rolling on a condom and covering it in lube while he watched. It seemed a little more intimidating jutting out from between Astrid's hips, but it wasn't as terrifying as he'd expected. And it was _Astrid._ She might be rough and playful and wrestle him for laughs, but she'd never _hurt_ Eret intentionally. And according to her, the guy she'd pegged recently had come from it, so she obviously did _something_ right.

Having a woman lean over him when she wasn't about to ride him looked a little strange, but Eret was more focused on the feel of slick toy pressing against him, the tip brushing against his ass and he tensed instinctively. Astrid didn't miss a beat, reaching for his erection and stroking him, distracting, relaxing until he felt the head stretching its way in. It wasn't unbearable, just uncomfortable. Astrid kept stroking his cock, slipping another inch in, then another, then another... and then she was _in,_ and Eret was shaking, thrown by the new fullness. He'd never appreciated the intimacy being _inside_ another person really could hold, not until someone else was inside him, toy or not.

"You alright down there sailor?"

Eret shifted, testing, and it really was alright.

"Yeah. Gentle though."

Astrid nodded in agreement, bringing his legs to rest either side of her. It was a little easier to relax that way, strange as the position felt for him still. She moved gently, one hand resting on his thigh while the other circled his glans, the dual stimulation inside and out making him quiver all over. The view of Astrid's still-bare body wasn't doing his mind any favours, easily distracted by the sway of her breasts, the way her teeth closed over her lower lip or her tongue poked out in concentration.

It took him a little time to get used to the feeling of being penetrated, but the toy she used pressed nicely against his prostate, that little hot-spot inside him Eret had not really known about until Astrid decided to go full steam ahead on the introductions. When he'd adjusted, Astrid started to speed up a little, reaching for his hand and pulling it down to his cock.

"I think it's hot watching a guy touch himself."

He wasn't going to argue; his cock was more sensitive than he could ever remember it being, every little brush making him shudder, the muscles in his legs starting to shake. Curving fingers around his shaft, Eret jerked himself in time with Astrid's thrusts, his free hand clutching a handful of bedsheet tighty while pathetic, needy whimpers and whines escaped his mouth. Instinct overrode inexperience, his feet planting themselves more firmly for leverage and his hips moving to get Astrid deeper, lower body rolling until his back curved.

A few more thrusts, a few more tugs at his cock and Eret felt the warmth in his belly expand, seeming to fill his whole body at once as his cock swelled and jerked in his grip, spurting come over his stomach and chest, the last drops running down the side of his hand as Eret gasped, breathless and groaning with the intensity of what he'd just experienced. He started a little blankly at his hand for a minute, only for Astrid to bring it to her mouth, little pink tongue slipping out of her mouth to lick him clean.

"Deep breath, this might feel a little strange."

Eret braced himself as Astrid pulled out, understanding the sound she'd made earlier despite saying she was fine; it felt strange to be empty after the fullness, and now his muscles had room to ache from the stretch of the toy. She undid her strap-on, took off the condom and moved to get Eret a towel.

As though proving herself right from earlier, Astrid wasn't acting any differently to before the sex. She wasn't implying he was less of a man for 'taking it' either, which he suspected he might hear if Eret started announcing he'd tried pegging. Not that he'd be broadcasting it, but... yeah, Eret was trying _that_ again some time. He wiped himself down, feeling the usual post-orgasm urge to take a leak and shuffling to the end of the bed, placing his feet on the ground.

"Whoa."

"Yeah. You'll probably walk like Bambi for a little while. Sit on soft things. You do get used to it though, should you get pegged more often. At least, that's what that guy said, and I got used to anal too. Only really aches for more than a day if the guy was _huge,_ rough or it had been a while."

Eret nodded as he stumbled, feeling like his legs had been replaced by leg-shaped jelly on the way to the bathroom. He peed, gave himself a quick rinse and went in search of his pants. Walking back felt a little easier, like he'd gotten used to being upright again. Astrid was waiting patiently, told him to entertain himself while she went for a quick shower and Eret meandered through her flat, sitting down a little too heavily on the sofa and wincing to himself. Well, she'd warned him... he shuffled a pillow under himself, and sat much more comfortably after, stealing another of Astrid's chocolates.

"So" Astrid came back out some fifteen minutes later, skin scrubbed pink and clean and a little missed moisture making her t-shirt cling to her hips "are we ok? Or are you gonna like, declare undying love for my ass and start hitting on me?"

"Really, nothing has changed for you?"

She nodded, chewing on one of her sweets and eyeballing him for evidence Eret had been snaffling them.

"Yep. I'm a little sore, a lot satisfied and I'm hanging out with my best friend. I am good. You?"

His _feelings_ toward Astrid hadn't changed - he still adored his best friend, and if she wasn't going to act differently, neither would he. He smiled, getting a toothy grin from Astrid in return.

"Yeah. We're good."

-HTTYD-

**FWB Eret/Astrid anal sex/pegging one shot... well, it kept me entertained to write.**


End file.
